My thoughts exactly. And I am afraid we are moving even further away from packages with this move..
caddy wants $1200 a year minimum, for 2 instances. For $1200 I'll give you a setup script for HAProxy/Certbot that will work on infinite servers, and will keep working next year without you paying me.
This is like the weird "SaaS all the things" model taken to the extreme.
Caddy performs worse, has crazy defaults (seriously, won't start when LetsEncrypt is down!?) and wants to charge you FOREVER to use their build service, even if you only use it once and never update.
So, tell me again who their target market is?